Hydrochloric Acid → 3-Methoxynaphthalene-2-boronic acid

Participants

Reaction Conditions

Reaction Steps

Under a nitrogen atmosphere, 15.0 g (94.9 mmol) of 2-methoxynaphthalene was dissolved in tetrahydrofuran (300 ml), and the solution was cooled to 0° C. After that, 238 mL (1.6-mol/L solution, 190 mmol) of normal butyllithium were slowly dropped to the solution. After the dropping, the mixture was stirred at 0° C. for 2 hours. After that, the mixture was cooled to −10° C., and 33 mL (340 mmol) of trimethyl borate was dropped over 10 minutes to the mixture. The resultant was heated to room temperature, and was stirred overnight. After that, 0.2N hydrochloric acid was added to the resultant to stop the reaction. Chloroform was added to the resultant to separate an organic layer, and the layer was washed with a saturated aqueous solution of ammonium chloride once and with water four times. After that, the solvent was removed by distillation, and heptane and toluene were added to the resultant residue to purify the residue by recrystallization, whereby 4.81 g of Intermediate Compound 6 were obtained.

Provenance & Evidence